ChemicalBook CAS DataBase List 5-(TERT-BUTYL)-2-METHOXYBENZENECARBALDEHYDE

5-(TERT-BUTYL)-2-METHOXYBENZENECARBALDEHYDE synthesis

5synthesis methods

Product Name:5-(TERT-BUTYL)-2-METHOXYBENZENECARBALDEHYDE
CAS Number:85943-26-6
Molecular formula:C12H16O2
Molecular Weight:192.25

100-97-0
7 suppliers
$14.00/250G

5396-38-3 Synthesis

5396-38-3
136 suppliers
$10.00/1g

5-(TERT-BUTYL)-2-METHOXYBENZENECARBALDEHYDE

85943-26-6
84 suppliers
$25.00/100mg

Yield:85943-26-6 68%

Reaction Conditions:

with trifluoroacetic acid at 80; for 16 h;

Steps:

32 Preparation of 5-(tert-butyl)-2-methoxybenzaldehyde

To a solution of 1-tert-butyl-4-methoxy-benzene (3 g, 18.27 mmol, 1 eq) in TFA (30 mL) was added methenamine (5.12 g, 36.53 mmol, 6.83 mL, 2 eq). The mixture was stirred at 80 °C for 16 hr. LC-MS showed desired compound was detected. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography (ISCO; 40 g SepaFlash Silica Flash Column, Eluent of 0~3% Ethyl acetate/Petroleum ethergradient 30mL/min). 5-Tert- butyl-2-methoxy-benzaldehyde (2.4 g, 12.5 mmol, 68% yield) was obtained as a yellow liquid. LC-MS analysis of the liquid shows the desired product's mass: m/z 193 (M+H) ¹H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (s, 9 H), 2.43 - 2.57 (m, 3 H), 3.89 (s, 3 H), 7.16 (d, J=8.8 Hz, 1 H), 7.63 - 7.73 (m, 2 H), 10.28 - 10.38 (m, 1 H).

References:

WO2018/132268,2018,A1 Location in patent:Page/Page column 109-110

2725-53-3 Synthesis